April 2026 was a banner month for the chess-playing Shahade siblings, WGM Jennifer and IM Greg. Late in the month, Greg appeared on Jeopardy!, where he dethroned Jamie Ding, who had won 31 times in a row! And April 7 saw the release of Jennifer’s new book, Thinking Sideways: How to Think Like a Chess Player and Win at Life, which is the topic of this post. A quick bio of Jennifer, in case you aren’t familiar with her: She is a three-time national chess champion, a two-time Global Poker Award winner and chess Olympic medalist, and a prolific author, with many more accomplishments in both chess and poker
In short, this is a lively, informative, and engaging book that I hope will garner a broad readership both within and outside poker and chess. There were a few poker terms that were unfamiliar to me as a non-player, but that did not detract from my understanding and enjoyment of the book. Similarly, there are no arcane chess references, and the insights from the chess world are explained so that anyone can follow them. I say the book is for everyone because, although there are fascinating anecdotes about both chess and poker, it is all in service to the author’s larger goal, which is to show how thinking sideways (“merging creative thinking with analysis”) works and how all readers can incorporate it into their own lives. Jennifer’s writing style makes it feel like she is talking directly to you (she actually does read the audiobook herself, which is a treat), even when you’re reading the book online or in print. She weaves in a number of anecdotes from her own life that illustrate thinking sideways. In one chapter, she even touches on her struggle with secondary infertility, a topic which is not discussed as widely as it should be.
As a companion to the book, I recommend Ben Johnson’s interview with Jennifer on his Perpetual Chess podcast. The two went to middle school and high school together, playing on the same chess team, which gives their conversations a familiarity that is delightful to listen to. My recommendation comes with a caveat, however. I am a big fan of all of Ben’s chess content—his podcast first and foremost; as well as his linkfest, a weekly mailing about chess-related content on the Internet; his book; and his book recommendations—so I felt it particularly regrettable that he made a joke about Jeffrey Epstein during the podcast. Ideally it would be edited out for the benefit of those who would find it triggering or simply in bad taste.
In addition to the release of Thinking Sideways on April 7, just a week before that, on March 31, US Chess named Jennifer its first official ambassador and announced that she and US Chess “wished each other well.” To understand the background of this, I recommend that you read her powerful Substack essay, the concluding paragraph of which begins “Whistleblowing is not for the faint of heart.” The chess community is lucky to have this creative, generous, and versatile player and writer who is not afraid to stand up as an advocate for us when needed.
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